Willem De Kooning was fascinated by America at an early age. He had an uncle who was a seaman with the Holland-American line who would tell him stories about the United States and once gave him an American football. According to his biographers, Mark Stevens and Annalyn Swan, "As an adolescent, de Kooning became fascinated with American pop culture. He loved jazz, Hollywood movies, photographs of girls in magazine advertisements. He would joke that he wanted to meet Constance Bennett and become 'rich and famous'... even as a child, de Kooning imagined leaving Holland - boarding a ship and simply vanishing. He dreamed of America the way other children dream of running away with the circus." (DK46)

Willem de Kooning secured his place as a stowaway on the ship that would take him to America - the S.S. Shelley - through the efforts of Leo Cohan. Cohan was the brother of the wife of Benno Randolfi's brother Franz. De Kooning had befriended Benno while studying at the Academie van Beeldende Kunsten en Technische Wetenschappen in Rotterdam. Prior to the U.S. trip, de Kooning had gone to Brussels around the spring of 1924, with Benno and another friend from the Academy, Willem (Wimpy) Klop. (DK49). De Kooning would later say about the trip, "I can't remember whether I went there [Brussels] to see any art... Because it was also connected with my wish to go to the United States, a sort of test of how long I could stay away from home. I found I could manage it for quite a long time." (DT) While in Brussels, de Kooning answered an ad in Le Soir and obtained jobs for himself and Wimpy at the van Genechten firm, a family decorating business not unlike Gidding and Zonen who he had worked for in Rotterdam. Benno had already returned to Rotterdam by that time. (DK50)

In late Autumn 1924 or early 1925, de Kooning returned to Rotterdam. For awhile he and Benno and Wimpy shared a tiny garrett at Karrensteegstraat 14 in the red light district. He also lived briefly at an apartment on the Krusisstratt, near the train station. The nearby Schiedamsdijk road and Katendrecht district were filled with bars, prostitutes and jazz playing dance nightclubs. With no steady source of income de Kooning would also stay on with other vagrants on a barge tied up at the docks. His sister Marie would sometimes drop off food packages for him at the barge although she rarely saw him at this time. She would drop off a package in the late afternoon and leave it for him to collect when he was able to. (DK54)

Unemployed and virtually homeless, de Kooning attempted to get a job on a boat or to stowaway on a boat without luck. In 1983 he would comment "I had a lot of trouble getting [to America]... Every time I hid out on a ship, they found me, or the boat wasn't going anywhere." (IK) Leo Cohan had worked on ships in the past and had already been to New York and wanted to return. But to get another job on a ship he would have to pay his union dues. He approached de Kooning and told him that if he paid him the 25 guilders he needed for his dues, he would arrange for de Kooning to stowaway aboard the next ship he got to America. De Kooning borrowed the money from his father but after giving it to Cohan, Cohan shipped out of town without de Kooning. Months later he reappeared, found de Kooning and told him that the S.S. Shelley was in Rotterdam to pick up cargo on its way to Virginia and that Cohan had been hired as a waiter on the ship. De Kooning could hide in the engine room but would not be able to bring many possessions with him, meaning he would have to leave his portfolio behind. Without time to alert his mother or his sister, Marie, de Kooning left Holland on July 19, 1926, hiding in the engine room on the S.S. Shelley. Although de Kooning would later say he left a note for Marie, she never received it. De Kooning had apparently disappeared without trace.